Pd-Catalyzed Aerobic Oxidative Biaryl Coupling: Non-Redox Cocatalysis by Cu(OTf)2 and Discovery of Fe(OTf)3 as a Highly Effective Cocatalyst

Dian Wang and Shannon S. Stahl

J. Am. Chem. Soc.,
2017, 139 (16), 5704–5707; DOI: 10.1021/jacs.7b01970


Pd-catalyzed aerobic oxidative C–H/C–H coupling of o-xylene is highly relevant to the commercial production of Upilex, a polyimide resin. In this work, the Stahl Group probed the role of a Cu-based cocatalyst in this reaction and showed that it does not play a redox role as is typically assumed for Pd-catalyzed oxidation reactions.

Mechanistic insights led to the identification of Fe(OTf)3 as an even more effective cocatalyst. The results of this study have broad implications for Pd-catalyzed C–H oxidation reactions that are now being investigated further in the Center.

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